ethyl-2-methyl-4-(2-methylphenyl)-4H-pyrimido[2,1-b][1,3]-benzothiazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: ethyl-2-methyl-4-(2-methylphenyl)-4H-pyrimido[2,1-b][1,3]-benzothiazole-3-carboxylate
• 英文别名: ethyl 2-methyl-4-(2-methylphenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate
• 化学式: C₂₁H₂₀N₂O₂S
• 分子量: 364.468
• InChiKey: WZKLIHVLEUWRHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 ethyl 6-methyl-2-thioxo-4-(o-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 丙戊酸 、 potassium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51 %的产率得到ethyl-2-methyl-4-(2-methylphenyl)-4H-pyrimido[2,1-b][1,3]-benzothiazole-3-carboxylate
  参考文献：
  名称：

  Pd-catalyzed regioselective tandem C-S/C-N bond formation for modular synthesis of pyrimidine-fused benzothiazoles from o-dihaloarenes and 3,4-dihydropyrimidin-2-thiones

  摘要：

  A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)2 as the precatalyst, Davephos as the ligand, and K2CO3 as the base, various 3,4-dihydropyrimidin-2-thiones with o-dihaloarenes proceeded smoothly, and the desired products were obtained in moderate to good yields

  DOI：

  10.1055/a-2311-3930

文献信息

• Colorimetric Metal Sensing of Fe³⁺ and Cr³⁺ and Photophysical and Electrochemical Studies Based on Benzo[4,5]thiazolo[3,2-<i>a</i>]pyrimidine-3-carboxylate and Its Derivatives
  作者：Shanthi Seenan、Sathiyanarayanan Kulathu Iyer

  DOI：10.1021/acs.joc.9b02297

  日期：2020.2.21

  detection of Fe3+ and Cr3+in acetonitrile solvent. Using measurements of absorbance intensity, the binding constants for the 4a + Fe3+ complex and 4a + Cr3+ complex were found to be 1.958 × 108 and 1.5442 × 107 M-1 with lower detection limits of 52 and 110 nM, respectively. 1H NMR titrations, Fourier transform infrared (FTIR) studies, electrospray ionization (ESI)-mass spectra, and Job's plots were used

  合成了含有电子给体和电子受体基团的苯并[4,5]噻唑洛[3,2-a]嘧啶-3-羧酸酯衍生物（4a-i），具有明显的光物理和电化学性质。评价了在各种阳离子存在下化合物4a的吸收性质的变化。化合物4a可以用作比色传感器，用于乙腈溶剂中的Fe3 +和Cr3 +的高灵敏度和选择性检测。使用吸收强度的测量，发现4a + Fe3 +络合物和4a + Cr3 +络合物的结合常数分别为1.958×108和1.5442×107 M-1，下限分别为52和110 nM。1 H NMR滴定，傅里叶变换红外（FTIR）研究，电喷雾电离（ESI）质谱和Job' s曲线用于验证4a + Fe3 +和4a + Cr3 +的特异性反应机理和比色传感。化合物4a在不同环境水样中的铁片加标样品中测定Fe3 +的结果令人满意，回收率高。
• Agar: a novel, efficient, and biodegradable catalyst for the one-pot three-component and green synthesis of 2,3-dihydroquinazolin-4(1H)-one, 4H-pyrimidobenzothiazole and 2-aminobenzothiazolomethylnaphthol derivatives
  作者：Ashraf Moradi、Reza Heydari、Malek Taher Maghsoodlou

  DOI：10.1007/s11164-014-1818-z

  日期：2015.10

  Abstract 3-(2′-Benzothiazolyl)-2,3-dihydroquinazolin-4(1 H )- one, 1-((benzo[d]thiazol-2-ylamino) (aryl)-methyl)naphthalen-2-ol and 4 H -pyrimido[2,1-b][1,3]benzothiazoles derivatives were prepared via one-pot three-component reaction of arylaldehydes, 2-aminobenzothiazole and isatoic anhydride or β -naphthol or ethyl/methyl acetoacetate in the presence of agar as a highly efficient homogenous catalyst

  摘要 3-（2'-苯并噻唑基）-2,3-二氢喹唑啉-4（1 H ）-一，1-（（苯并[d]噻唑-2-基氨基）（芳基）-甲基）萘-2-醇和在芳烃存在下，通过芳醛，2-氨基苯并噻唑与异丁酸酐或 β- 萘酚或乙基/甲基乙酰乙酸的一锅三组分反应制得4 H- 嘧啶并[2,1-b] [1,3]苯并噻唑衍生物 琼脂作为高效均质催化剂。使用无毒且可生物降解的催化剂以及高收率，较短的反应时间，简单的后处理和绿色条件是该方法的最重要优点。图形概要
• Pd-catalyzed regioselective tandem C-S/C-N bond formation for modular synthesis of pyrimidine-fused benzothiazoles from o-dihaloarenes and 3,4-dihydropyrimidin-2-thiones
  作者：xuying hu、ruiqi Liu、shiwen Fu、Lianxu Shi、Chunxia Chen、Jinsong Peng

  DOI：10.1055/a-2311-3930

  日期：——

  A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)2 as the precatalyst, Davephos as the ligand, and K2CO3 as the base, various 3,4-dihydropyrimidin-2-thiones with o-dihaloarenes proceeded smoothly, and the desired products were obtained in moderate to good yields